Abstract
ABSTRACT
One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH
2
P
+
Ph
3
Cl
-
, were subsequently treated with Br
2
/Et
3
N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH
3
CN-H
2
O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.